The effect of the change of synthetic route on the product 20859-23-8

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SDS of cas: 20859-23-8. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: (S)-2-Bromosuccinic acid, is researched, Molecular C4H5BrO4, CAS is 20859-23-8, about Synthesis and Evaluation of Novel TLR2 Agonists as Potential Adjuvants for Cancer Vaccines. Author is Lu, Benjamin L.; Williams, Geoffrey M.; Verdon, Daniel J.; Dunbar, P. Rod; Brimble, Margaret A..

Cancer immunotherapy has gained increasing attention due to its potential specificity and lack of adverse side effects when compared to more traditional modes of treatment. Toll-like receptor 2 (TLR2) agonists are lipopeptides possessing the S-[2,3-bis(palmitoyloxy)propyl]-L-cysteine (Pam2Cys) motif and exhibit potent immunostimulatory effects. These agonists offer a means of providing “”danger signals”” in order to activate the immune system toward tumor antigens. Thus, the development of TLR2 agonists is attractive in the search of potential immunostimulants for cancer. Existing SAR studies of Pam2Cys with TLR2 indicate that the structural requirements for activity are, for the most part, very intolerable. We have investigated the importance of stereochem., the effect of N-terminal acylation, and homologation between the two ester functionalities in Pam2Cys-conjugated lipopeptides on TLR2 activity. The R diastereomer is significantly more potent than the S diastereomer and N-terminal modification generally lowers TLR2 activity. Most notably, homologation gives rise to analogs which are comparatively active to the native Pam2Cys containing constructs.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”